Sending, receiving, and organizing email in Outlook.com
If messages still go to Junk Email after you've selected Never Block Sender and Never Block Sender's Domain, first verify the safe-sender entry directly in Outlook.com rather than relying only on the right-click option.
Go to Settings → Mail → Junk email → Safe senders and domains
Add the sender's full email address, select OK, then click Save. Also check Blocked senders and domains to make sure the same address or domain hasn't been added there by accident. Don't move addresses/domains in Outlook.com's Safe Senders list to Junk Email.
For a message that's already in Junk, select it and choose Report → Not junk (or It's not junk). Microsoft notes that doing this also provides feedback that helps improve Outlook.com's filtering.
If the sender is already listed under Safe senders and domains and new messages still go to Junk, check the actual sender address in the message headers. Sometimes the visible From: address isn't the same address being used behind the scenes; for example, newsletters and automated services may use different sending addresses or mailing-list infrastructure.
Also check Settings → Mail → Rules for anything that could be moving those messages. I recommend checking Inbox rules when mail isn't arriving where expected.
If none of those explains it, could you provide the following from one affected message, with your personal address removed:
From:
Return-Path:
Authentication-Results:
In particular, the Authentication-Results line can help determine whether SPF, DKIM, or DMARC authentication is failing. If multiple legitimate senders are affected, not just one sender/domain, please mention that as well.
If everything is configured correctly and Outlook.com continues putting mail from a confirmed Safe Sender into Junk, you can contact Outlook.com support through Help → Still need help? → Yes. Microsoft provides that route specifically when the documented Outlook.com junk-mail steps don't resolve the issue.
References:
Mail goes to the Junk folder by mistake
Filter junk email and spam in Outlook
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